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<h1><a href="https://archiveofourown.org/works/28058034">Memories Served</a> by <a class='authorlink' href='https://archiveofourown.org/users/AnotherWorld3111/pseuds/AnotherWorld3111'>AnotherWorld3111</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Angst, Crossdressing, Dean Winchester Wears High Heels, Dean Winchester Wears Makeup, Dean Winchester Wears Panties, Dean Winchester Wears Women's Clothes, Feminization, Feminized Dean Winchester, I love these tags, Implied/Referenced Homophobia, Insecurity, M/M, Past Dean Winchester/Other(s), cuz we love that dash of</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-12-13</td></tr>

<tr><td><b>Updated:</b></td><td>2020-12-13</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-10 15:52:57</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>2,118</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/28058034</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/AnotherWorld3111/pseuds/AnotherWorld3111</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>It was bought on a whim. He might as well carry on with it – on a whim.<br/>So he does, and Dean dresses up – for himself, at first. But then Cas helps, and maybe it doesn’t have to be just for himself?</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester</td></tr>

<tr><td><b>Comments:</b></td><td>8</td></tr>

<tr><td><b>Kudos:</b></td><td>82</td></tr>

<tr><td><b>Collections:</b></td><td>Destiel fics I like</td></tr>

</table>

<a name="section0001"><h2>Memories Served</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><ul class="associations">


        <li>
            Inspired by

            <a href="https://archiveofourown.org/works/25252246">Rockstars and Pharaohs</a> by <a href="https://archiveofourown.org/users/vulcanarmr/pseuds/vulcanarmr">vulcanarmr</a>.
        </li>
        <li>
            Inspired by

            <a href="https://archiveofourown.org/works/1082534">Winchester's Rouge</a> by <a href="https://archiveofourown.org/users/almaasi/pseuds/almaasi">almaasi</a>.
        </li>
        <li>
            Inspired by

            <a href="https://archiveofourown.org/works/6596353">beyond the cheap colored lights</a> by <a href="https://archiveofourown.org/users/streamratqueen/pseuds/streamratqueen">streamratqueen</a>.
        </li>

    </ul><blockquote class="userstuff">
      <p>At this point you can trust me to make my fics come with a “fics like this” kinda option with how many fics ‘inspire’ a single one of my own<br/>Ao3 get on doing this so I don’t have to look like an oddball tagging so many fics in mine<br/>That being said, above listed fics are great and worth a read go check them out<br/>Anyway<br/>Un-beta’ed, typed this on my phone within half an hour, any and all mistakes are mine, I’m sorry not sorry but i just needed some dean crossdressing for ages</p>
    </blockquote></div><div class="userstuff module">
    
    <p>Dean stared at the bag in his hand. It had been far too long, and he’d really only bought it on a whim. Neither meant he actually had to go through with his plan. Clearly, he’d just been thinking in the heat of the moment, passing by the shop on the street when he was alone, no one around to judge… Swallowing, he looked around himself, as if his surroundings might’ve changed in the past half hour he stood, scrutinizing the nondescript bag in his hands. But nope, still in his room in the bunker, the door was still comfortably closed and locked, and since everyone that needed to sleep had long since gone to bed, Dean was fairly certain that no disrupting moose would demand his presence anytime soon.</p><p>And they still had several boxes of cereal left, so Jack would also be occupied for a bit.</p><p>So… that was that. Everyone around was doing their own thing, and he could just put the bag away, never to be seen or thought of for several years, and he could go to bed and sleep, wake up tomorrow fresh-eyed and showing no hints of the dilemma he was going through right now…</p><p>Or he could man up and… Dean snorted at himself with the choice of words. A bunch of other phrases flitted through his head, from ‘no time like the present,’ to ‘an opportunity as rare as this…’ </p><p>Trust the one phrase he’d thought to himself decades ago to do the trick.</p><p>And Jesus, Dean thought as he gently put the bag on his bed. Had it really been decades since he’d gotten to do something like this?</p><p>All too aware he was distracting himself with his internal rambling, Dean studiously kept it up as he took the packaged items out of the bag. </p><p>The last time… wasn’t as memorable as when he was alone, dad off hunting by himself, testing Dean to do his own thing with the coordinates he’d sent his son, and Sam at Stanford – no, he wasn’t going to think about his brother right now, bygones were bygones when he was unwrapping–</p><p>Redirecting his thoughts, he continued the stream of almost nonsensical dialogue in his head.</p><p>The last time wasn’t easy to remember because Dean didn’t know then that it would be the last time – until now. Each moment was just as likely to be the last, so he’d savored every moment as much as he could, but the time when he felt truly alone was when he’d gone all out.</p><p>Decked head to toe in matching colors, even his face a brilliant work of art… that night would forever be seared into his mind. Maybe a top ten moment of his life, Dean mused as he brought the familiar material up his legs. He sighed, eyes closed and thoughts momentarily adrift as he sunk into the sensation of the material against his legs. He’d prepared himself first, of course he did, his thoughts were enough to distract him if he did it right, so the time he’d spent had flown by, and now, there wasn’t any drag against the silk. It slid up smoothly against his thighs before it settled in place, and he took another moment to just luxuriate in that sensation alone before he continued.</p><p>His mind brought up the abandoned stream of thought, as if it had never broken into disruption in the first place. </p><p>The last time had to have been… almost a decade ago, and the amount of years he calculated almost caused a painful pang in his throat. God, it really had been too long, how did he manage to forget, to live without even a single night of indulgence, in feeling that constriction around his chest as he laced himself up?</p><p>Sweeping the now empty packaging off his bed, he brought out one of the smaller bottles from the bag. This, like shaving, would take some time, but unlike shaving himself, would need more focus, more care. Hands steady with guns were not the same with makeup, so he made sure he was as comfortable as he could be, lounging on his bed without allowing himself to get distracted by the stockings straining around his legs, the corset tightening momentarily before he settled, the way he’d reclined showcasing the beautiful arch of his soles and the muscles that stayed tense in his calves with the long stilettos adorning his feet… </p><p>Swallowing, he twisted open the bottle and meticulously began applying the contents on his nails. Soon, he was pleased to discover that it wasn’t as hard as he thought it would be. Around two decades since he’d gotten to do this, and he thought he’d have gotten rusty…</p><p>Thoughts of the club in Florida kept his mind entertained until the polish dried, and then he was soon afterwards dismayed to realize that he had, in fact, gotten rusty, but more upsetting was the fact that this was at something he used to consider himself a pro at, once upon a time.</p><p>“Dammit,” he hissed, wiping away the smudges of the eyeliner. Tears clouded his vision with frustration when he realized that he’d have to redo the eyeshadow again, and he let the eyeliner clatter to the sink as he dropped it, clutching porcelain edges as he fought to control himself. After hours of silence, his muttered curse and the plastic bottle still rolling around in the basin had shattered the silence, continuing to stubbornly echo loudly in his room.</p><p>There was a hesitant knock on his door. </p><p>“Dean?” Cautious and hesitant, the voice was quiet, as if unwilling to disturb the rest of the bunker’s occupants, while still being loud enough to pierce through the wooden door and reach through to Dean inside. </p><p>“Fuck,” he mumbled, even as he found himself striding over to the door. At least his body still remembered how to walk in these, which wasn’t as great as it should’ve been when his elongated legs ended up eating the distance faster than he wished. </p><p>He only just brought himself to still his hands before he pulled the door open. </p><p>“Cas?” He questioned, wondering what the angel was doing outside, even as he cursed himself for forgetting–</p><p>“I heard noises,” Cas’s voice was still low, unsure but a comforting rumble that vibrated through Dean’s chest as he went on. “I thought everyone was asleep but… I just wanted to check, is everything alright?”</p><p>Mind at war, he quickly chose and cast away various arguments. The winners for both sides were shame, primarily, but it was still being defeated by the fact that this was Cas, and above everything, after everything, Dean knew Cas wouldn’t care. </p><p>He pulled the door open.</p><p>To Cas’s credit, he didn’t flinch, or outwardly react in any negative way otherwise. What he did do was pause, and tilt his head, squinting as he regarded Dean’s face. “Your lines are uneven,” he finally announced.</p><p>“No shit, Sherlock,” Dean grumbled, but like he’d uttered some sort of secret password, Dean opened the door wider, allowing Cas in. “I thought I’d still have the hang of it, but apparently, my hands don’t remember how to make two straight lines anymore,” he grouched, going back to the sink to pluck the eyeliner again. </p><p>His mind was, (not?) for the first time tonight, choosing to be unhelpful by fixating on the one thing he was trying hard not to think about; with the stilettos on, he was several inches taller, even more taller than Cas, and the way Cas had to tilt his head back to meet Dean’s eyes made him think of other circumstances where Cas would have to look up at him, one where they’d be closer instead, Dean’s arms around Cas’s neck as he straddled–</p><p>Flushed and fighting to steady his breathing, Dean turned around, leaning against the sink.</p><p>“I could help you with that?” Cas offered. “As an angel, my hands don’t shake unnecessarily…” he trailed off, as if it only just occurred to him that straight lines weren’t exactly straight when they were on someone’s eyelids, but apart from raising his eyebrows, Dean mentally shrugged, and held the bottle of eyeliner to Cas. </p><p>This thoughts warred with each other again, trying to make Dean focus on something he didn’t want to; there was one prominent way this would end up, and instead of Cas’s hands around his waist, pulling Dean in by the corset, it would be delicately balancing the eyeliner instead… </p><p>“Go ahead,” Dean offered, too late realizing he sounded challenging.</p><p>Cas didn’t back down, though. Taking it, he took his time inspecting it, as if analyzing it would teach him how to make the perfect wing on each side, and then he was done, and was striding forward, glitching Dean’s brain by trapping him against the sink–</p><p>“Uh,” Dean didn’t know where to look, those eyes, that was already concentrating, those plush lips, parted slightly and exhaling tiny puffs of air against Dean (he was an angel, did he really even need to breathe?), or those hands, raising to bring the eyeliner to Dean’s face?</p><p>“Stay still, please,” it was an order, Cas commanding as gently as a battle hardened warrior could do, before he began applying the eyeliner, and Dean only just reminded himself to freeze – who was he kidding, there was no conscious thought to freezing, his body taking over and closing his eyes but also emanating <em> what the fuck? </em> as he felt wet liquid dragged across his eyelid.</p><p>The process barely took longer than a handful of minutes. Dean was far too disappointed when Cas stepped back when he was done, taking his warmth away with him. The sound of the eyeliner being closed brought him to his senses enough for him to blink, eyes feeling wet, and he turned around, regarding himself in the mirror.</p><p>Well. If he ever had another night like this, screw everything else. He was definitely going to make Cas do the eyeliner for him, no matter what. He’d deal with his cock, straining to embarrass himself, just like he was right now, keeping his waist pressed to the sink.</p><p>“Looks good,” Dean commended, eyes taking himself in further, even though he didn’t need to. Behind him, Cas was silent for only a second.</p><p>“You look… exquisite, Dean. Whether or not my hand was of any help.”</p><p>Dean’s mind was his own when he thought of how else Cas’s hand could be of actual help, but his body went one step ahead without permission and turned around.</p><p>Dean swallowed again, feeling ashamed – no, bashful, he wouldn’t be ashamed, but he could be – he could be embarrassed, his own flesh was making a fool of himself – but he wasn’t a fool, a-a clown, or anything else he hadn’t heard directed at his face, but he knew was said, when they thought he couldn’t hear, when they felt he wouldn’t retaliate because Dean may have looked <em> pretty</em>, but his muscles and calloused knuckles still spelled <em> fighter</em>, and a fighter that <em> won </em> his battles, no matter how his body portrayed itself.</p><p>At the moment, his tongue was still fighting a war of its own, deciding whether to side with his mind or body.</p><p>“Yeah?” He asked, shyly instead – <em> demure</em>, demure he could do, he remembered how to do that, and Cas must’ve picked it up, must’ve picked something up, because he suddenly stepped back into Dean’s space, looking a little more confident even as his eyes squinted, requesting explicit consent – or an explicit denial. </p><p>Dean was twenty years past denying the little things, and every year he’d learned to accept increasingly bigger things. This year, he was looking at the biggest of all wins, and after everything, how was he still expected to say no?</p><p>Like he ever could in the first place.</p><p>Nah, he’d won that battle ages ago, and Dean would be damned if he broke that particular streak right now.</p><p>“Yes,” Cas breathed out, placing the bottle of eyeliner on the sink behind Dean. “Your soul is divine, Dean, yet however your body is built is a work of art on its own. But how <em> you </em>chose to express yourself, how you are right now… it is truly an honor to be allowed to see you like this.”</p><p>Dean smiled. “You’re not limited to just seeing,you know.”</p><p>Cas’s eyes was as sharp as he was, and Dean knew the second – when the words had barely just gotten out of his mouth – when Cas understood what Dean was offering – that Dean was offering it all.</p><p>And Cas took, with explicit consent offered alongside Dean on a silver platter.</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>Drop your thoughts in the comment box below, please?</p></blockquote></div></div>
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